What Jared Kushner's Time at the Observer Can Tell Us About How He'll Advise Donald Trump

The news that Jared Kushner and his wife, Ivanka Trump, are house hunting in Washington, D.C., makes it all but certain that Kushner will have some sort of advisory role—official or unofficial, depending on the stringency of federal anti-nepotism laws—in his father-in-law's incoming administration.

That kind of role won't be anything new, of course. By all accounts, Kushner was Trump's de facto campaign manager and behind-the-scenes confidante during the tumultuous election season, and he continues to wield influence throughout the equally shaky transition process.

What else can we expect from this 35-year-old political parvenu, real estate developer, and newspaper owner, now that he has stepped into a position of power more vast than he ever could have imagined before Trump announced his candidacy by gliding down a gilded escalator in Manhattan? Kushner's stewardship of The New York Observer, the small but influential weekly newspaper he purchased in 2006 for a reported $10 million, gives some insight.

Here's a look at how his tenure at the publication may help explain aspects of Trump's unusual march to the White House.

KUSHNER IS COMFORTABLE WITH TUMULTUOUS LEADERSHIP

At the Observer, Kushner has overseen six editors in 10 years. When Kushner hired Ken Kurson, a journalist, Republican operative, and close family friend, in 2013, the paper saw its sixth editor in chief in just seven years. From the late Peter Kaplan, who stepped down amid looming staff cuts in 2009, to Tom McGeveran to Kyle Pope to Elizabeth Spiers to Aaron Gell and on to Kurson (whose four year run is the second-longest in the paper's history, after Kaplan) the Observer's masthead has been in flux pretty much continuously since Kushner took over.

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(Full disclosure: I worked at the Observer from February 2013 to February 2016. I only met Kushner once, since he spent most of his time at 666 Fifth Avenue, where Kushner Companies is headquartered.)

The constantly shifting leadership speaks to a kind of managerial impatience on Kushner's part, a trait reflected in the conveyor belt of campaign directors who filtered through Trump's team during the election. According to reports, Kushner was partly responsible for ousting Corey Lewandowski and Paul Manafort, both former campaign managers with checkered pasts, during the election season.

Now that the transition is underway—if plodding along—reports have also suggested that Kushner pushed for Chris Christie's ouster from the transition team, too, payback for Christie having successfully prosecuted Kushner's father, Charles, while he was New Jersey's attorney general. (Kushner, in the only interview he's granted since he joined Trump's campaign, toldForbes that this isn't the case.)

HE WAS CONSTANTLY TRYING TO DO MORE WITH LESS

Sound familiar? Trump earned billions in free media and spent about half as much as Clinton throughout the campaign, a strategy that paid off. Although Trump spoke repeatedly about the frugality of his efforts, he was also aided by a like mind in Kushner, who helped direct a bare-bones data team "designed to unify fundraising, messaging and targeting," as Forbes put it. Kushner may have honed his ability to run a lean operation through his penny-pinching at the Observer. In 2009, for instance, Kushner fired the Observer's cleaning woman, and the history of the paper under his ownership has been one of downsizing—though his political efforts appear to have been more successful.

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To be sure, the Observer is not the only media outlet that has been through rounds of cost-cutting and downsizing over the last decade. The paper's top brass speak enthusiastically of online traffic records, but current and former staffers say that morale is low due to repeated staff cuts, erratic management and the paper's waning popularity among the audience it once catered to.

Kushner speaking at the Commercial Observer 2016 Power Gala in June, 2016.

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The influence the paper used to wield, as a kind of alternative weekly for New York's elite, has declined significantly if not entirely since Kushner bought the publication from its founder, Arthur L. Carter, a former investment banker, in 2006.

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HE LIKES TO TINKER BUT HE SEEMS TO LACK AN OVERARCHING VISION

Since 2006, Kushner has changed the format of the paper repeatedly—from a broadsheet to a tabloid back to a broadsheet back to a tabloid. Aside from cosmetic changes and the occasional bid for a hatchet job (he famously tried to commission a takedown of Dick Mack, a real estate executive with whom Kushner had a beef ), Kushner appears not to have had much of an editorial vision for the paper.

Since Kurson has come on, the paper's tone—once smart and acerbic—has become increasingly muddled, a strange mixture of bland fashion and lifestyle content, pro-Bernie Sanders pieces, Russian propaganda, and long articles that have taken on Kushner's family foes, such as New York attorney general Eric Schneiderman, who sued Trump for defrauding consumers with his university in 2013 and became the subject of an Observerhit piece the next year. (The Schneiderman piece has a tortured history and was a source of embarrassment to many at the paper.)

The Observer has also published glowing profiles of those in Kushner's family orbit, such as his brother-in-law Eric Trump, who was described in the headline of a 2013 article for the paper as "New York's Young Philanthropist Powerhouse."

As one former staffer for the Observer put in an email to me, Kushner "doesn't have many core convictions, which explains why he kept changing the format of the paper and reversing himself, but in some ways, that can be seen as openminded." The staffer adds, "He likes to shake things up and grab for the new idea, but then gets bored. It's his version of decisiveness. At the same time, he's very guarded and calculating, which should serve him well in the Trumps' inner circle."

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HE SHARES HIS FATHER-IN-LAW'S DISDAIN FOR THE PRESS

Trump's hatred of the press—particularly his scorn for The New YorkTimes and CNN—needs no introduction. And though he may not tweet about it, Kushner reportedly shares his father-in-law's disregard for reporters. As one former Observer editor told theNew Yorker, "He hates reporters and the press. Viscerally."

Kushner did not buy the Observer because he loved the salmon broadsheet and wanted to nurture its sometimes loving, often critical view of the New York elite. In fact, he told New York magazine that when he bought it, "I found the paper unbearable to read, it was like homework."

So why acquire it then? Some have speculated that it opened doors for Kushner that he might not have been able to step through as the 25-year-old successor to a disgraced New Jersey real estate mogul. But Kushner was reportedly frustrated that he couldn't turn the paper around more easily. He toldNew York in 2009 "I didn't expect the public side of this. And I didn't expect to be walking into this at the worst time to be buying newspapers."

Jared Kushner with Barry Diller and Wendi Murdoch at a media event in 2008; Kushner purchased the Observer in 2006.

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Curiously, Kushner also didn't want to offload the paper once he understood the scope of the challenge. Former Observer editor Elizabeth Spiers has writtenabout her short-lived efforts to raise funds to buy Kushner out. Kushner's response to her offer was resolute: "He said absolutely not, and seemed almost offended by the idea. The only explanation that seems plausible to me is that he didn't particularly enjoy owning the paper—but he didn't want anyone else to own it, either."

KUSHNER WILL CUT HIS LOSSES IF HE HAS TO

Just three days after Trump's shocking victory, The New York Timesreported that the Observer had ceased its print edition. Its last issue was published Wednesday, November 9. Joseph Meyer, the Observer's CEO (and Kushner's brother-in-law), told the Times that the move reflected a broader focus on the publication's national online audience, and that Trump's victory had nothing to do with the decision.

But it was hard not to see it that way, based primarily on the timing. (Kushner's spokespeople did not answer email questions about his plans for the future of the paper.) To an outsider, it would seem that Kushner had tired of his days as a newspaper owner, moving on to the greener and greater pastures of the White House.

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